


F-ing 101

by littlegreenfish



Category: Once Upon a Time (TV)
Genre: Alternate Universe - College/University, Anal Sex, Dom/sub, F/M, Femdom, Light Bondage, M/M, Multi, Pegging, Threesome
Language: English
Status: Completed
Published: 2014-03-16
Updated: 2014-11-07
Packaged: 2018-01-15 22:45:33
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 13,537
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1322035
Author URL: https://archiveofourown.org/users/littlegreenfish/pseuds/littlegreenfish
Summary: <blockquote class="userstuff">
              <p>Before Professor Mills took him home, college junior Killian Jones would have never, not in a thousand years, let anyone bend him over. Now? He's not so sure, and finds himself getting fucked more regularly than he attends class. In short: College AU: Killian gets fucked a lot, and learns that he loves it. There’s not really much more to it than that.</p>
            </blockquote>





	1. The Professor: Ms. Cora Mills

Killian Jones wasn’t sure if he liked his classes, or even the idea of college. It didn’t seem like  _anyone_  could get a job, degree or not, so why spend the money? He wasn’t sure if he liked a lot of things, but he knew two things for sure.

The first was that he  _loved_  women.

If nothing else, that made his classes bearable. There were beautiful women  _everywhere_  and he wasn’t picky.

The second was that he  _hated_  the Dean of Students. Mr. Gold called Killian into his office at least twice a semester to tell him that he might not have what it took to go to the university. That he would have to try harder if he wanted to get anywhere in life. That he needed  _direction_. 

If it wasn’t for Mr. Gold’s lack of belief in him, Killian probably would have dropped out a long time ago. Unfortunately, he was determined to prove to the other man that he could succeed, and so he stayed in school.

That really sucked, because he  _hated_  school.

His love of women coupled with his hatred for the Dean of Students was probably what fed his attraction to Gold’s ex-wife, Ms. Cora Mills.

The first time he saw her it was only in passing, and he didn’t really know who she was. He did a double-take because she was beautiful, but once he realized that she was too old to be a student, he moved on. The last thing he needed was for Mr. Gold to call him into his office and fire him for fraternizing with a professor.

Then, he learned who she was.

She was Mr. Gold’s ex-wife, and that changed everything. 

Suddenly it didn’t matter that she was old enough to be his mother. What mattered was that her blouse was usually  _just_  unbuttoned enough that when she bent over to tell him what he’d done wrong, he could see down her shirt. 

The class didn’t matter. It was some dumb intro to literature that focused on fairytales. Killian was a junior. He hadn’t taken an intro course in awhile—but for Cora, he was willing. For Cora, his cock ached at night and he licked his lips during class thinking about her sweet, sweet cunt. 

Killian Jones was, in fact, so transfixed on Professor Cora Mill’s breasts and cunt that he didn’t really pay attention in class. Apparently it showed, because less than a month into the semester, she called him to her office.

Elated, Killian was quick to respond to the invitation. 

“Professor?” He said as he walked into the older woman’s office, his accent thick and dropping because he  _knew_  that women liked it. “You wanted to see me?” 

“I did.” Cora was sitting behind her desk, straight as an arrow. Killian could barely see down her shirt—it was disappointing. “Do you know why you’re here?”

“Because I don’t pay attention? Because I’m a distraction? Because I don’t do my work?” Killian threw out the reasons why other teachers and professors had called him out in the past. He was much more focused on Cora’s lipstick, and idly wondered what it would look like smeared on his shirt. 

“How seriously or not seriously you take my class is not my problem.” Cora leaned forward, and there they were—her beautiful, beautiful breasts. He could almost see them. “The problem is that you are letting yourself get  _distracted_  with things that are,”

The professor paused, and licked her ruby led lips.

“ _Inappropriate.”_

“Is that so?” Killian asked, moving his gaze up to her face.

“This isn’t a game,  _Mr. Jones_ , and I’m no fool.” Cora leaned back in her chair and crossed her arms. “Do you really think you’re the first student to stare at me?”

“Of course not. I imagine you’ve always gotten looked at.” Killian wasn’t sure what Professor Mills was getting at, but he liked where their conversation was going.

“And where do you think that’s going to get you?” She asked, cocking an eyebrow. “Do you think that staring at your professor—disrespecting her as an educator and turning her into some sort of sex fantasy—is going to get you anything but a failing grade?”

“I’m perfectly aware of my actions.” He smiled. “But if you were really so uncomfortable, then why not call me out in class? Surely that would be a better way to teach me a lesson.”

Cora laughed.

“Attention is exactly what you want—why would I do something so idiotic? Honestly, you stupid little boy. What do you take me for?” She met his gaze again. “I’ve seen countless young men exactly like you come and go. Young, handsome idiots without a care in the world who think they can have whatever they want.”

“I’m afraid I don’t understand the point of your lecture, Professor.” Killian was quickly growing bored. He hated being judged. “If all you’re going to do is insult me, I think that I’ll take my business elsewhere.”

“Oh, I’m going to do much more than that.” Cora stood and leaned across the desk, taking Killian’s chin. “I’m going to teach you a lesson.” 

“Is that so?” Killian breathed out, focusing on her lips. “And what are you going to teach me, Professor Mills?”

“If you do exactly what I say, I’m going to fuck you. Do you think you’re capable of that?”

“Aye. I…I think I can manage it.” Cora was going to fuck him. The thought made him half-hard where he sat. Was this real? If it was a dream, he didn’t want to wake up. Not until he’d buried himself between the older woman’s legs.

“Good.” Pulling back, Cora turned and grabbed her coat and purse. “Come with me.”

“Absolutely.”

Not realizing that he was acting like a kid with candy, he followed Cora out of her office, down the hall, and into the parking lot.

A few minutes later, they were in her car and moving away from campus.

“This is really going to happen?” Killian asked, licking his lips and looking over at Cora. 

“If you listen to me, then yes.” The professor reached over and gave Killian’s leg a squeeze.

“Fantastic.” He couldn’t keep a grin off of his face. This was actually happening. He was going to fuck his professor—Mr. Gold’s ex-wife.

 _Awesome_.

By the time that they were standing in Cora’s apartment, Killian’s head was full of ideas about what he was going to do to the former Mrs. Gold. As soon as the front door was closed, he was leaning forward to start kissing the back of her neck. 

“Not yet.” Turning around, she put a hand on his chest and pushed him away. 

“Not yet?” He echoed, brow furrowed, hands on her waist. 

“I told you. If you want to do this, then you have to listen to me. You need to obey  _everything_  that I say, or you’re out the door with no way home.”

“Yeah?” The idea of letting the older woman call the shots was surprisingly appealing. Wasn’t this what a lot of fantasies were made of? Come to think of it, Killian was pretty sure he’d watched a few pornos with the exact same plot 

If he was right, he was going to have his face between Cora’s legs sooner than later, and that suited him (and his aching cock) just fine.

“Mmhm.” Cora moved her hand up so that she was pressing a finger to his lips. “Not a word while I tell you what to do. Understand?”

He gave a small nod, his gaze dropping down to her blouse.

“Good.” A smirk on her lips, she moved her other hand to start unbuttoning her blouse. Killian’s mouth started to water. “Like most boys your age, I’m sure that you’re  _filthy_. Some women like that,”

She paused and shrugged out of her shirt, letting it fall to the floor. 

“I however prefer my men clean. Go down the hall. Third door to the right, you’ll find a bathroom. Shower, and be _thorough_.” Reaching up, she pulled a pin out of her hair and sent it cascading down her shoulders. 

Killian swallowed hard.  With her hair up and her blouse buttoned, Cora looked like the sexy teacher that every schoolboy dreamed about. 

With her hair down and her shirt off, she looked  _magnificent_. 

“When you’re finished, you may join me in the bedroom.There will be no need to redress. Do you understand me?” 

Killian opened his mouth to speak, and then hesitated. He wanted to say something witty, but didn’t want to risk getting kicked out of the apartment. 

She smiled, and he relaxed, relieved. 

“Good boy.” She crooned, and he was again aware of how uncomfortably tight his pants were. “You may answer me.” 

“Yes.” He said immediately, doing nothing to hide how hard she was making him. 

“Oh—that reminds me.” She reached out and hooked her fingers in the front of his t-shirt, pulling him in so that she could whisper in his ear. “If you don’t want to find yourself walking back to campus all alone, you will answer my questions with “yes ma’am” or “no ma’am”. You will only address me as “Ms. Mills”. Can you do that?” 

“Yes  _ma’am_.” He whispered back, his heart racing. He’d never let a woman take the lead like this before, but he’d also never fucked one of his professors. There was a first time for everything. 

“Good. Now get going.” A hand on his waist, she turned him around and gave his ass a soft slap to move him forward. “Third door to the right. When you’re done, I’ll be in the bedroom. The door will be open. While you’re at it, get rid of that thing in your pants. I’m going to need you to last more than five minutes.” 

Not about to linger and ask questions, Killian almost ran down the hall, pulling off his shirt as he went. By the time that he was in the shower and the water was on, his hand was on his cock and he was furiously jerking off to the thought of getting between Cora’s legs.

That woman on top of him—wet and willing and ready and saying  _good boy_  and— 

It turned out that Cora’s estimate of five minutes had been an enormous exaggeration. The orgasm hadn’t been all that good—it had been quick, it didn’t matter, what would matter was what it felt like to come inside of Mr. Gold’s ex wife—but it brought him one step closer to bedding his English professor.

Grabbing a bar of soap, he thought back to what she’s said. Be thorough? What did that even mean? Leaning back against the wall of the shower, he quickly soaped his chest, his hand moving down towards his crotch. 

Maybe she’d had a point. It had been a few days since he’d showered.

After making quick work of giving  _everything_  a rinse (he was having sex after this, right? So even his ass had to come up smelling like a rose, or else she’d have a reason to kick him out) he stepped out of the shower and grabbed a towel. Tying it around his waist, he glanced into the mirror. 

A quick tousle of his hair—and  _perfect_. No woman could resist that.

“Ms. Mills?” He called out as he entered the hall, making a beeline for an open door that had to be the bedroom.

“If you don’t hurry, I’ll finish without you.” Her voice carried down the hall, and Killian’s cock stirred beneath the towel that he was still wearing. 

As he reached the doorway, he paused so that he could stare. 

Girls had dressed up for Killian before. It was something he actually really liked. He’d gone to frathouse Halloween parties with Red Riding Hood on one arm and Sleeping Beauty on the other. He’d bought cheap-ass lingerie as apology gifts and torn it off of willing cheerleaders the next day. 

He fucking  _loved_  it when girls did stuff like that just for him.

He’d expected Cora to maybe dress up a little while he was in the shower—put on some sexy glasses and some heels, really play up the professor thing.

Instead, she was just as he’d left her: in her bra, pencil skirt up to her waist and hair down over her shoulders. Despite all of his fantasies while he’d been showering, he wasn’t disappointed. She still looked amazing.

A slow smile appeared on her face, and she beckoned him forward.

“Very nice.” She said appreciatively, her hands on his hips as she looked up at him, an eyebrow raised. “Now that you’re here, are you ready for more rules?”

“Yes ma’am.” He drawled, grinning and moving forward into her grasp.

“Number one: you will continue to answer my questions with “yes ma’am” and “no ma’am”. Number two: you will continue to refer to me  _only_  as Ms. Mills.”

She pulled the towel down, giving his half-hard cock an appreciative glance.

“Number three: you will obey every command that I give. If you question or refuse me, you will be punished.”

“Number four: if you want something, always use your manners.”

“Number five: once we are finished—if you behave—I will drive you home. If you ask to stay, you will be made to walk. 

Number six: if you want me to stop, just start talking about my ex-husband. That should be enough to kill the mood.” She looked up and met his gaze. “Am I clear?” 

“Crystal, Ms. Mills.”

“Wonderful.” Standing, she cupped his face and pulled him down into a kiss.  _Finally_. Groaning appreciatively, he tangled his fingers in her hair and opened his mouth, pleasantly surprised when she met him with equal force, her nails raking down his back. 

“Careful!” Killian hissed, breathless as Cora pushed him back against her bedroom wall, perfectly manicured fingernails digging into his ribcage.

“Why? Afraid that I’ll break you?” She teased, pressing her lips just under his chin.

“No, ma’am.” Laughing, he leaned down just slightly so that they could press their mouths together, his hands dipping down to grip her by the hips. 

“Good boy.” She whispered, reaching down and giving his cock a quick jerk. Moaning, he pushed his hips forward. “Undress me.” Her lips moved to his neck, and he couldn’t help but grin. 

Reaching behind her, he unhooked her bra and let it fall to the floor. She hummed appreciatively against his neck and bit down hard. Groaning, he moved down to unzip her skirt, leaving the professor only in her underwear. That was gone a few seconds later, and they were both naked.

Pulling Cora into another kiss, he moved his hand up to her chest, his cock hard against her thigh. She met his advance eagerly, her fingers in his hair as she pulled him further down. He couldn’t believe that he was doing this—fucking his English professor, the ex-wife of the man he hated more than anything.

She pulled away and took a few steps backwards towards the bed. He took it as an opportunity to look at her, and nearly came on the spot. Her lipstick had rubbed off against his face and neck, but her lips were still red thanks to how they’d been kissing.

Her breasts were fucking  _perfect,_ and her hair was messy from how he’d been grabbing it. She looked just as good breathless in bed as she did lecturing on the Grimm brothers.

A coy smile making its way onto her face, she spread her legs and looked from his face to her cunt.

“You know what to do.”

Even though it was only about ten feet from the wall to the bed, he almost broke into a run, dropping to his knees in front of the bed. He put his hands on her thighs and leaned down with his mouth open.

“ _Wait_.” She said sternly, grabbing his hand again. “Ask for permission.”

“Really? A—“ It only took a quick glance up to realize that she was serious. Killian had been in her classes, and knew to take her threat to kick him out if he disobeyed her seriously. “…can I?” 

“Can you what? That doesn’t sound very polite, Killian."

”Can I eat you out?”

“Try again.” She teased, and it was fucking  _painful_  how hard his cock was without her cunt in his face to distract him.

“Ms. Mills, can I  _please_  eat you out?” 

“Better.” She let go of his hair, and he moved his head down to press his open mouth against her. She was already wet, and he gave a few long, appreciative licks over her arousal to get the taste of her in his mouth. Her moan was her reward, and he was quick to move up to her clit, rubbing his tongue against it hard a time or two before pulling back to drag his tongue along her cunt.

Loving how aroused she was, he blew lightly against her arousal. He felt her shiver, and a moan escaped his lips. He started to move one of his hands up, but paused. 

“I—Ms. Mills?”

“Yes?” She looked down at him, one hand still in his hair.

“May I use my fingers?” He asked, swallowing and licking his lips. 

“You may.” She paused. “You agreed to obey my every command. Did you mean it?” 

“Yes ma’am.” He responded immediately, giving her cunt a quick kiss and rubbing his fingers briefly over her clit before popping them into his mouth to get them wet.

“Good.” She paused, and leaned back against the bed, her legs still off the mattress. “Then make me come.”

Holding back a whimper, Killian pulled his fingers from his mouth and moved his hand between her legs. Leaning back down, he pressed his open mouth between her legs again. 

She was still wet, and his fingers went in easy. Curling them, he started to move them slowly against her, his tongue matching the pace of his hand. At first, Cora was somewhat relaxed against him, letting out an occasional sigh or moan. 

Gradually, he started to move his fingers faster. His lips moved up to her clit, and he moved his tongue against it, kissing it with just as much passion as he’d given her lips. Cora’s breathing became more erratic, and the hand in his hair became painful as her fingers dug into his scalp and she pulled his head forward. 

If he’d been with another woman, he might have pulled away just to tease her. With Cora, he didn’t dare do anything that might make this end.

He knew that she was going to come when her legs tensed up on either side of him and there were suddenly  _two_  hands in his hair. He started to move even faster, and his free hand moved up to her hip.

A few short minutes after that, Cora Mills let out the most delicious noise that Killian Jones had ever heard. He could feel her tighten around his fingers, her body tensing and relaxing with every wave of her orgasm. He didn’t relax or let up until he felt her body still completely.

Part of the reason for it was that until she was done, Cora held his head in place. When he finally pulled back, he was panting hard and his arousal was inconveniently painful. She sat up slowly and cupped his face so that he had to look up at her. Her face was flushed. 

“Good boy.” She whispered, and he had to grab the base of his cock to stop from coming. “Are you ready for your next instructions?” 

“Yes, ma’am.” He breathed out, his voice somewhat hoarse as he licked his lips, still able to taste her.

“That’s what I thought.” She stood on slightly trembling legs, pulling him up with her. The evidence of her arousal was still glistening between her legs. He couldn’t wait to fuck her. “Bend over the bed.” 

“I…what?” He asked, cracking his fingers (they were somewhat sore after what he’d done) and looking at her, obviously confused.

 “Don’t question me.” Her voice was venom, and he was apologizing before he even knew it. 

“I’m sorry—I’m sorry  _Ms. Mills_. “ He said rather quickly.

“I know you are.” She put a hand firmly on his back and pressed down. “Now, knees on the ground. Bend over.” A little reluctantly he did as he was asked, wondering what she had in mind. “Forehead to the mattress. Close your eyes, don’t look, and don’t ask questions.” 

He almost asked why, but stopped himself before it was too late. Closing his eyes, he listened hard and tried to figure out what his professor was doing. He heard what sounded like a box opening followed by some rustling and a quiet ripping noise. Then, she was behind him again, and he heard a bottle open. 

“Tell me, Killian, have you ever been fucked?”

“What?”

“Has anyone ever fucked you?” 

“I’ve been with plenty of women  _Ms. Mills._ I thought that was obvious.”

“Don’t take that tone with me.” She’d slapped his ass  _hard_  before he could say anything else, and he was too stunned to do anything but reach down and grab his cock again to stop from coming before he’d even gotten inside her. When  _was_  he getting inside her? “Has anyone ever  _fucked_  you?”

Her hand moved down to his ass, her fingers wet against his—

“The hell are you doing!” He almost rolled over, but a firm hand against his back stopped him. 

“If you were so opposed to it, you would have started talking about our dear Mr. Gold.” Cora rubbed her lubricated fingers against his hole, and he shuddered.  _This_  was something that only a few girls had ever done, and even then it had been in passing while they were blowing him in an attempt to make him finish more quickly. It always worked. “Now, do you want me to stop?” 

“No, ma’am.” It came out as a whimper, and he felt his face go red.

“Good boy.” She pushed a finger in, and he buried his face in the crook of his elbow. “Has anyone ever done this to you before?” 

“Yes, ma’am.”

“How much?” Her other hand moved down to grip his cock, and he wasn’t sure which way to push his hips.

“Just…just a finger. Like this.”

“My, my. How boring. And here I thought you were going to be quite adaring lover.”

“I am!” He growled into his elbow, shifting slightly as she put in another finger. This much had been done to him before, but not for a long time. He’d forgotten that he liked it.

“That’s good. Because if you lacked a sense of adventure, then you wouldn’t let me fuck you.”

“Ms. Mills, you can do whatever the hell you want to me.” Killian groaned into the mattress, pushing back against her. She was gripping the base of his cock hard—he couldn’t have come even if he wanted to, even though it fucking  _hurt_.

The fingers didn’t hurt, though, especially when she curled them just right and—

“Oh my  _god—“_ He twisted his fingers furiously in the sheets and bit down so hard on his lower lip that he could taste blood.

“No, not god.  _Goddess_.” She corrected, chuckling quietly as the third finger went in. That one did hurt a little, but he didn’t care. Cora was going slowly and using plenty of lube, and only added a fourth finger once he’d relaxed again. It burned, but he didn’t care. 

“Ms. Mills, I’m starting to get the idea that you’re not going to let  _me_  fuck  _you.”_ He said eventually, tensing up as she spread her fingers. 

She laughed outright at that, and pulled out her fingers. 

“As if you’re worth that. No. But this is  _far_  better, don’t you think?”

He felt what had to be a strap-on rubbing against his hole, and his breath hitched. He felt the head of the toy (it didn’t feel  _too_  big, thankfully) pressing against him, and it took all of his self-control not to push back and try and take it in more quickly than she was offering.

“Answer me.” Her voice was low and dangerous, and he’d never been so fucking aroused in his fucking life. 

“Yes, ma’am.”

“Tell me what you want me to do.  _Ask_  me for it.”

“I want it.”

“You want  _what_? What do you want me to do, Killian?” It was so close to being in, but a hand on his lower back was stopping him from rocking backwards and taking it in too soon.

“Please fuck me. Please fuck me, Ms. Mills.” He muttered through gritted teeth, shame flooding his face. He’d never felt so humiliated—except maybe when Mr. Gold called him into his office—but he’d also never felt so good.

“You’re such a filthy boy, Killian.” She laughed, pressing forward. It finally went in, and he nearly pulled back. It wasn’t as big as he’d expected, but it was bigger than her fingers and less flexible and it _hurt_. “Letting yourself be fucked like this.” 

“Boys like you like to call girls who do this names, don’t they, Killian?” She crooned as she started to move. He could feel her add more lube, and he was relieved. “Things like  _slut_?” 

“Y-yes, ma’am!” He pushed back slightly against her.

“Tell me. What other names do you call them?” 

“Whore, dirty, hooker—“

“That’s right, Killian. And now you’re one of them. You’re a filthy, filthy slut.” She paused, and pushed in further than she had before. He cried out—it hurt, and it felt  _good_  because it was in  _just the right fucking spot_ — “Say it. Say that you’re a slut.”

She spanked him again, and he found himself wishing that she’d do it again. She did, and he drew a ragged breath before following through with her command. 

“I’m a slut!” He cried out, unable to help himself. How had this even happened? He fucked women! They didn’t fuck him. He wasn’t like that. He wasn’t gay, he wasn’t fucked up he was a fucking  _player_ , but his English professor was fucking him and it felt so fucking  _amazing_.

“That’s right, you stupid little boy.” She laughed, and it was music to his ears.

She started going faster. He imagined that she would have been more rough if they’d done this before, but it was his first time being penetrated like this and he wasn’t sure that he could have taken it. On that note, it was clear that Cora knew what she was doing. That she’d done this before. 

Had she done it to Mr. Gold?

The thought of the Dean of Students getting fucked up his ass was so satisfying that Killian decided if he didn’t come soon, he was going to die.

“Please!”

“Please, what?” She teased, moving in  _just_  the right way.

“Let me come.” He whispered, entire body shaking as he was continually denied release.

“Again. Be  _polite_.” She gave an especially hard thrust to get her point across, and he actually felt a few frustrated tears on his face.

“Please let me come. Ms. Mills, please let me come.” He groaned, the words quiet. Just because he had to say them didn’t mean that they had to be loud.

“I can’t hear you.” She gave his ass another hard slap. “ _Louder_.” 

“Ms. Mills, please let me come!” He cried out, because anything would be worth an orgasm.

“Good boy.”

She  _finally_  started moving her hand over his cock. Before he could think of anything else, he was seeing white and coming hard, his entire body shaking with what was hands down the most satisfying orgasm of his entire life.

Her thrusts slowed, and she pulled out.

He was left panting on the bed, his ass aching and his legs weak. It took quite a lot of effort, but he managed to turn around and move so that he was lying on his back, staring up at the ceiling. Cora had left the room. He could only assume that she was coming back soon. 

When she returned, she was wearing a robe and holding a glass of water and what he could only assume were painkillers. His clothes were tucked under her arm. “Here.” She stood in front of him.

He sat up in bed, wincing, and took the water and the pills, downing them both in one go. 

“Now get dressed, and I’ll drive you home.” 

Right. That had been one of the rules. Really, Killian was just glad that he didn’t have to walk. As far as he could tell, the game was over, so he flashed her a cheeky grin and cocked an eyebrow.

“Yes, ma’am.”

 


	2. The Quarterback (David Nolan)

**Summary for the Chapter:**

> Killian gets fucked again. Oops.

**Notes for the Chapter:**

> The next chapter is also for her, but I tried to make this chapter extra good as a birthday present to GraveVyxen!! HAPPY BIRTHDAY!!!!!!!!!! I was going to write her the Milah chapter for her birthday but she already knows how that's going down--so I figured that this would be more of a surprise!! Incidentally, Milah is next.

 The next day, Killian decided to skip class. It wasn’t that he felt bad about what he and Cora had done (he felt good, but a little confused) but he was sore and didn’t want to give Ms. Mills that satisfaction if they passed in the hallway. He still couldn’t believe how easily she’d gotten her way. He’d never, not _ever_ let a woman boss him around like that before.

Even thinking about it made him want to jack off.

He didn’t go to classes the next day, either. Why not make it a four-day weekend? By the time that Saturday rolled around, he was feeling good, if not a little emasculated. He’d done a little googling, and what he’d found was infuriating. 

Letting a beautiful woman stick it up him didn’t mean he was even a little gay. He’d never even kissed another guy—not even thought about it. What Cora had done with him had nothing to do with other men.

He would’ve done just about anything to be able to say that he’d slept with Ms. Mills. 

It had been insanely easy to decide that he deserved some time off, so as soon as the weekend was in full swing Killian was off campus and at one of his favorite bars. It wasn’t anything to write home about—just a little hole in the wall that was grungy and dark and kind of dirty. 

 _The Jolly Roger_.

It was usually full of musicians and artists and hipsters—a few lesbians every now and then. Killian liked it. He knew the crowd as well as they knew him. Ruby Lucas, the beautiful bartender, had a drink ready for him as soon as he was at the bar.

It was easy enough to tell when someone didn’t belong at The Jolly Roger. They usually left sooner than later, and absolutely never came back. As Killian made himself comfortable at the bar with his rum and coke, he looked around for one or two of his favorite ladies. 

Emma Swan? He’d never actually made it past one dance with her, but that didn’t matter. It _really_ didn’t matter, because she wasn’t there.

Regina Mills? Also absent. Come to think of it, Killian hadn’t seen either of them in a few weeks, ever since they’d had a very public and very drunken fight a few weeks prior. Maybe they’d been kicked out.

Ruby was busy at the bar. It didn’t look like she had time for a quick squeeze in the bathroom. Too bad.

As soon as he’d eliminated his usual targets, Killian began another survey of the room, looking for new faces. New tits. New cunts. 

A not-so-new face stopped him in his tracks as he looked to the other end of the bar. What was the quarterback doing anywhere near The Jolly Roger? Surely _The Rabbit Hole_ was more to his tastes. 

Killian stared for another long minute, squinting and wondering whether or not his eyes were playing some kind of trick. Nope. David. It was David Nolan. David Nolan did _not_ belong there. 

It didn’t look like there were any beautiful women unattended, and so Killian decided that harassing one of the most beloved faces on campus would have to do until more people filtered in. Setting down his empty glass, he took a few quick steps to where the other man was sitting and slid into an empty stool next to him.

“What’s the resident Prince Charming doing in a place like this?” He asked, a smirk on his lips as he held out his hand for his second drink, nodding a quick thanks to Ruby.

“Excuse me?” Brow furrowed, David turned to him. It looked like the football star was holding onto his miller light for dear life.

“I’m talking to you.” Killian said slowly, forcing down the urge to roll his eyes and laugh in the other man’s face. “I haven’t seen you here before, and I spend more time here than just about anybody.” 

“Well,” He paused and bit his lip. “…I haven’t been here before. I usually—“

“The Rabbit Hole?”

“How did you know?” He actually looked surprised.

“Your whole crowd goes there.” Killian waved a hand dismissively.

“My crowd?” David asked with the gall to look offended.

“The football team, the cheerleaders—your cute little marching band groupie.” Killian paused, and glanced around the bar. “…forgive me, but where _is_ your flautist?”

“Her _name_ is Mary Margaret.” David said a little too defensively, color high in his cheeks. “…and I’m not sure if she’s _my_ anything.”

“Oh no. Trouble in paradise?” Killian asked, gesturing for more drinks. If he couldn’t get laid, he might as well get some blackmail on the quarterback. It could get him out of a tight squeeze later, like the time he broke his wrist trying to get a peek at Emma Swan’s window.

“No relationship is paradise.” David muttered, accepting the drink and taking a few long gulps.

“Fair enough.” Killian relented. “…one of the many reasons why I avoid them at all costs.”

“Well, they’re hard but…they’re worth it.” David shrugged. “I love her. A lot.”

“Again, something I try to avoid. You’re only young once, after all.”

“So why waste it without love?” 

“Because love means only one set of tits, and frankly I’m not willing to settle for that.” 

“Well, I guess we’re going to have to agree to disagree.” With a heavy shrug, David took a long drink. Killian was surprised. Usually the other man was defensive and protective when it came to his values. The break up must have been bad.

“So what happened?” He asked, not bothering to hide his curiosity.

“Why should I tell you?”

“Who else are you going to tell? And who am _I_ going to tell?” 

A long pause, and then David continued.

“I made a mistake.” 

“Do elaborate.” 

“I hooked up with Kathryn.” 

“Cheerleader Kathryn?” Killian asked. As the college’s most eligible bad boy, he was making his way down the pyramid.

“Yes.” David almost looked like he was about to cry.  Killian decided to throw him a bone. Reaching out, he gave the other man a pat on the back.

“If it’s meant to be, you’ll work it out. If you break up once or twice it’ll make a better love story, if nothing else.”

“You think?” David asked, meeting Killian’s gaze. “You think she’ll take me back?”

“I can’t say. But if you really love her, then I don’t see why not.”

“Thank you.” David cracked a smile. “I…” He looked long and hard at the man in front of him. “I’ve seen you around before, but I don’t think that we’ve ever formally met.” 

“Of course not.” Sticking out his hand, Killian flashed a winning grin. “Killian Jones. You may have seen me wrapped around a cheerleader or two. Or three.” 

“Killian Jones.” David repeated slowly, and then his eyebrows went up. “Mary Margaret’s cousin broke your nose!” His eyes narrowed, and he eyed the other man suspiciously. “She said that you came onto her pretty strong for a stranger.” 

“Too much whiskey. Miss Swan and I are on better terms now.” Killian quickly assured the football player. It was a lie. “But now that I think about it, maybe a night away from the ladies would be good for the both of us.” 

“Guy’s night now?” David asked, looking as simple as two plus two. “I usually only do that with the guys. The football team, I mean.”

“I’m so sorry that you have to settle. I usually don’t do it at all. The cheerleading squad is more to my taste.”

David smiled again, and Killian looked at his lips for just a little too long. 

“Next round’s on me.” David announced, and Killian cheered him on.

An hour later, Killian knew far too much about the quarterback’s sex life, but he’d also let a few dirty truths of his own slip. It didn’t really matter. He had enough rum in him to make anything funny, and he was finding that despite how much of an idiot David was, he wasn’t a bad drinking buddy. 

“I just don’t know what to do to get her back.” He slurred, looking at Killian like a kicked puppy. “I’d do anything to get her attention. I just…I just…she ignores me. Won’t talk to me. Won’t _look_ at me.” 

“You want to get her attention?” Killian echoed, cocking an eyebrow. “That’s it?” 

“That’s it.” David agreed. “Or at least not want her attention for about two seconds. I can’t stop thinking about her. I know things will be okay, but right now they’re _not_ , Killian. They’re not.” 

“No worries, mate.” His body humming, tingling, and very warm, Killian once again focused on David’s lips. “You could forget about her for a few minutes and get the whole bar talking, you know.”

“Really?” David asked, and suddenly he was about a foot closer. 

“Mmhm.” Before he could regret the thought, Killian was tangling his fingers in David’s hair and pressing their lips together. It wasn’t something he’d have ever done sober, but god damn did it feel _good_. David’s lips were chapped and his chin was itchy, and he was kissing the _hell_ out of Killian and _fuck_.

“Boys—boys!” Ruby’s voice cut in at least five minutes in. Killian’s lips felt heavy, and he liked it. He wanted more.

“Want a turn?” He slurred, pulling back to look at Ruby.

“You don’t have to go home but you can’t stay here unless you keep your pants on.” Ruby paused, and looked them up and down.

“Do you want to keep your pants on?” Killian asked matter-of-factly. He was in control enough to know that he was about to have the great college experiment. Earlier that day he might have spurned the idea, but it had been just long enough since his second drink for that thought to go out the window. 

“Not really.” David shook his head, and with one glance down Killian could see that he was already hard.

“Got a car?” Killian asked, even though he already knew the answer. Everyone knew about David’s rich stepfather. Of course he had a car.

“Yeah.” David nodded enthusiastically.

“Then let’s go.” Grabbing David by the front of his shirt, Killian pulled him off of his stool and towards the door.

Ruby was laughing on them, but the joke was on her. She wasn’t going to sleep with the quarterback. Killian was. And that would be enough dirt to get every cheerleader’s phone number, bra size, and favorite summer shandy. 

That would make it worth it, and that would make that they were going to do not gay at all. 

At first, they didn’t even make it to the parking lot.  David pushed him up against the old brick wall of the Jolly Roger as soon as they were out the door. Moaning openly, Killian let the other man start in on his neck.

Eyes closing, he reached down and slipped his hands into the other man’s back pockets so that he could give a solid squeeze. He’d never groped another guy’s ass before.

It was kinda nice.

He shoved his leg forward, and could feel the quarterback’s erection through his jeans. A few weeks ago that would have repulsed him, but now it made his own arousal throb and he almost melted back against the dirty building.

“Fuck…” He muttered, squirming when David bit down on the crook of his neck. There would be bruises. He’d have to remember this until they went away.

“You don’t taste like a lady.” David pointed out, and Killian laughed even as David was unbuttoning his pants. “Can we just do it here?” 

“No.” Killian couldn’t stop smirking as he pulled David into a rough kiss, opening his mouth against the athlete’s and shoving his hips forward. David was incredibly fit and strong. Killian didn’t think that he’d ever had anyone grip him so tightly. 

“Why not?” David asked. There was whiskey on his breath. Killian could taste it with every kiss, and he wanted more.

“Because…” Killian whispered, breath ghosting over David’s ear and making him shiver. “If you take me to your car, I’m going to let you fuck me.”

David’s breath hitched and he nodded a few times. 

“Alright.” Smirking, Killian gave David a small push, slapping his ass as he hurried towards his car. “That’s more like it, _Prince Charming_.”

It turned out that David didn’t have a car: he had a truck. That suited Killian just fine, even if it was a little cramped under the truck’s canopy. At least they had their privacy. It was already getting hot in the cramped space, but that added to how ridiculous what they were doing was. 

There were already some sleeping bags thrown down. Killian imagined that his companion had gone through a romp or two in the past thanks to his truck. The idea that pretty little Mary Margaret had been boned where he was kissing David only added to the thrill.

David was never going to be able to forget about this as long as he had this truck. Killian was going to make sure of that.

He had the quarterback on his back. Killian was straddling him as best he could, his mouth hot and wet and open against the other man’s chest as he hastily unbuttoned his shirt. His own shirt had come off as soon as they piled into the truck. 

This wasn’t like a woman at all. No breasts, for one thing—but David still moaned and pushed up when Killian got to his nipples. 

“You like this?” Killian gave one of them a light pinch, and David’s back arched against the bed of the truck.

“ _Jesus_ , Killian, just…just…” 

“Don’t worry, you’ll get what you want—as long as I get what I want.” As he spoke, Killian unbuttoned David’s jeans and pulled them down. The other man let out a grateful moan, and Killian took a long moment to stare at how hard the other man was through his boxers.

Of course they were covered in little footballs. _Of course_.

“What do you want?” David asked, biting down on one of his knuckles as he pushed into Killian’s palm. Touching another man’s dick was weird as hell, but the quarterback was acting way more needy than any woman Killian had ever been with.

He _liked_ that. He _liked_ how helpless the other man was under his touch.

“If you suck my cock, I’ll let you fuck me. If you have lube, I mean. I’m not doing it without that.” Killian had only been penetrated the one time, but he knew enough about what had happened to not underestimate the important of getting ready.

“I—I’ve got some back here, but…”

“But what? Too straight to suck my cock?” Killian pushed his own jeans past his hips and kicked them off, falling onto his side next to David. Getting out his cock, he rubbed his thumb over the head and made eye contact with David. “I think we’re past that.”

“I…I don’t…”

“Neither do I, but this is what college is for, right?” He pulled the quarterback into another long kiss, and felt his resistance give way. “It’s only once.” 

“Yeah.” David swallowed hard, and looked down between Killian’s legs. “I—I mean…if it’s only once, I…”

“Come on.” Killian sat up as best he could. The canopy wasn’t very high and he had to hunch over, but he’d hooked up under less comfortable situations. “In your mouth. Now.” 

The football star almost looked like he was going to object, but apparently thought better of thinking at all, because a few seconds later his mouth was around Killian’s cock. 

“Fuck…” Killian hissed, his fingers tangling as best they could in the other man’s short hair. It was obvious that David had no idea what the hell he was doing, but his mouth was _so_ hot and tight that nothing else mattered. “Watch your teeth!” He added. “You’ve seen plenty of girls do this, I’m sure—you know what to do.”

It almost sounded like David offered an objection, but it was hard to tell with his lips around Killian’s dick. Licking his lips, he watched as David did the best he could. He was moving slowly, but taking a considerable amount of Killian’s arousal into his mouth considering that it was his first blowjob. 

“Just like that…” Killian groaned, pushing David’s head down every now and then to help him get the hang of it. “Now…” He licked his lips, and thought about what he was going to say. “I’m going to let you fuck me, but you have to do exactly what I say.” He whispered, his voice low with arousal. “You don’t have to do it, that’s fine. But if you don’t let me do it, then you don’t get to fuck me.”

David gave a sort of affirmative grunt and pulled back to give the other man’s length a long lick that made Killian shiver with pure fucking delight.

“What do I have to do?” The other man asked, his words rushed and his face red. 

“You have to let me come on you.” Killian was rather enjoying calling the shots. It was just what he needed after his night with Cora. “Can you do that?”

“Yeah. I can do that.” David promised. “Are you close?” 

“Get on your back.” Killian put a hand on the other man’s chest and pushed him down, straddling his chest. The other man’s cock was pressing against the curve of his ass, hot and heavy and _nothing_ like silicone. Killian didn’t want to admit it, but he couldn’t wait to have the quarterback inside of him. Just to see what it would feel like, he reached behind himself and gave the other man’s cock a few quick jerks.

David fucking _whimpered_ , and that was the end for Killian.

He was going to come on the other man if it was the last thing he did—ruin him and mark him and make him _never, ever forget this_.  Grinning, he gripped his own arousal and started moving his hand, eager to see what the other man would look like once he came.

“Tell me to do it.”

“What?” David asked, pushing his hips up so that his cock rubbed up against Killian’s ass again. The other man’s hands were gripping his hips tight enough to bruise. Part of Killian hoped they would.

“Tell me to come on you.” Killian growled, his voice more authoritarian than before. “Now.”

“I…” David faltered for a moment, swallowed hard, and then continued. “Come on me.” He whispered, sounding horrified. 

That was enough. That fucking did it. Biting down hard on his lower lip, Killian gave himself a few final jerks. Even though it was just his hand, his orgasm hit him hard, especially when he saw his release hit the other man’s chest. They were both panting hard, and it was clear that David was itching for his own satisfaction. 

“Don’t worry, you’ll get yours.” Killian dragged his finger down the other man’s soiled chest. He brought the finger to his lips and gave it a slow lick. “Where do you keep the lube?”

“Here!” David was so excited that he almost through Killian off.  He reached under one of the sleeping bags and pulled out a bottle, pressing it into the other man’s hands. “Here.” 

“I’m not going to do it. _You’re_ the one reaping rewards.” Killian pushed the bottle back. The last thing he wanted to do was admit that he was curious about how the other man’s fingers would feel inside him. They’d be rougher than Cora’s—maybe more clumsy, too. 

Less patient. 

He wanted to feel it.

Lucky for Killian, he didn’t have to wait long. Apparently David was too eager to argue, and soon enough there were wet fingers between his legs. Killian clasped a hand over his mouth to stop from moaning as one and then two fingers were inside of him. 

It turned out he’d been right. He was sure that David had fingered more than a few cheerleaders in his illustrious career, but not like _this_. There was a little hesitation, but mostly his fingers were just fucking _spreading him open_ before he even knew he was ready for them. It hurt a little, and it burned a little, but he didn’t care.

Killian pushed back down on the fingers, wanting to get them deeper. He was biting down hard on his fingers to keep quiet, and his legs were almost shaking as the third finger went in to the last knuckle. “David…” He groaned, unable to help himself as he leaned down and pulled the other man into a rough, salty kiss.

They were both sweaty and the truck didn’t exactly smell _good_ , but he didn’t care. All that mattered was that soon there was going to be something inside him. He was half-hard by then even after his first orgasm, and more than ready for a second as soon as possible. 

“Okay, okay!” He finally breathed out, unable to take anymore. 

“Okay?” David asked, breathless and staring up at Killian with wide eyes.

“I said okay!” Killian groaned, pulling David’s hand away, slathering his own hand with lube, and grabbing the quarterback’s cock. He briefly moved up onto his knees and then went back down. He could feel it against his hole. 

His body didn’t really want to give in, but Killian _needed_ this. It took a few rotations of his hips, but soon enough he felt the other man go in. David was bigger than the toy Cora had used. At least thicker. That was fine. Killian liked the way that it hurt.

As soon as he was in, David let out one of the most needy, pathetic, pitiful moans Killian had ever heard. He wanted to hear it again.

“Does it feel good to have your dick in another man?” He asked, grabbing the quarterback’s chin so that they had to look at each other.

“Does it feel good being fucked by one?” David retorted. Killian almost slapped him, but instead decided to kiss him. His fingernails were digging into the other man’s ribcage. He wanted to leave marks.

Marks that Mary Margaret just might see and blame on Kathryn. 

The way that they were moving against each other was a little awkward, mostly because Killian just wasn’t used to being fucked, but they figured it out. It was too slow for either of them, but they were doing their best given their location and experience with other men.

“Fuck, okay, okay—“ Killian eventually hissed, tired of how difficult it was to ride the other man. This wasn’t anything like a rodeo. “Just get on top of me.” Rolling off of the quarterback, he got on his back and kept his legs spread, pointedly looking away as David settled between his legs. 

This time it was David controlling how fast he went in, and a ragged moan ripped itself from Killian’s throat as the other man pushed in suddenly and without warning.

“Fuck _that—“_ He almost whimpered, pushing down against David’s hips. “Just fucking do it don’t wait don’t stop just _fuck_ —“ He hadn’t been meaning to talk so much, but the quarterback’s hips were pounding against his ass and it fucking _hurt_ and he needed _more_ of it.

Reaching down, he started to desperately jerk himself off, his hand moving in time with the other man’s hips. He should have known that David would have this much endurance. Sports and all. 

Cora hadn’t been able to move like this. It was a whole new experience, and Killian found himself becoming undone.

When he came, his orgasm shook him like a fucking earthquake and his chest ended up just as messy as David’s. As he rode it out, his hips moving down erratically against the other man’s thrust, the quarterback didn’t slow down at all.

There were already bruises forming on Killian’s hips. David was pulling him down hard so that their hips were flush, his own starting to stutter in their movements as he tried to reach his own orgasm.

“Fuck. Fuck. _Fuck_.” David was grunting like an animal with each hard thrust, and Killian was letting out ragged gasps. Now that he’d finished, his body was much more in tune with what was going on.

His throat, his hips, his ass—everything felt more sensitive and raw, and the pain wasn’t quite as delicious as before. That didn’t make it bad, however, and Killian found himself letting out a reluctant whimper at David’s final round of hard thrusts. 

The other man’s hips eventually came to a stop. David let out a long, low sound and held Killian’s hips down, shaking like a leaf as he finished. A few more thrusts just to make sure he was done, and then he pulled back and collapsed next to the other man.

Panting hard, they both stared up at the truck’s canopy.

“So.” Charming started, clearing his throat.

“Just a one time thing. Just to try it. We don’t have to talk about it.” Killian was slowly realizing that he’d done something as gay as the day was long, and there was no talking his way out of it.

Whatever. Girls were still better.

“Yeah. Cool.” David hesitated, and then looked over at Killian. “Look, so…I can’t drive, obviously…so I’m probably going to just sleep it off here. I don’t know what you?...”

“Don’t worry, mate. Your integrity is safe with me.” Killian laughed, legs only shaking a little as he started to pull his jeans back on. His briefs were long gone in the tangle of sleeping bags. “I’m going home.” 

“You sure?” David asked, brow furrowed. “I could call you a cab, or…or something.”

“I’m not a freshman girl drunk on wine coolers and making poor decisions.” Killian pulled on his shirt next, his movements sluggish. “I know what I’m doing.”

“Alright.” David agreed. “I…I’ll see you around.”

“Maybe.” Killian agreed, kicking open the door to the back of the pickup. “Want this closed?” He asked, scooting forward and ignoring the ache in his ass.

“I guess.” 

“Alright. Well, goodnight.” Killian slid out of the back of the pickup and slammed the door shut. It was more awkward than he’d though it would be to stand, but that didn’t matter. Not sure what to do or where to go, he took a few long and slightly painful steps toward the bar before settling on sinking down in front of a “Customers Only” parking sign. 

He could sit here for a while and wait for his buzz to go away a little more.  That was fine. Pulling out his phone, he looked at the time. It wasn’t even one. He shouldn’t be this tired.

Just as he was about to get back up, one of the most expensive cars he’d ever seen anywhere near The Jolly Roger pulled up. The window rolled down, and he came face to face with what had to be one of the most beautiful women in the world. He knew he’d seen her before, but where?

“Hello, Killian.” She smirked, looking at him with laughing eyes. “Do you want to come home with me?” 

“Who are you?” He asked, trying to remember where they’d met.

“Get in and I’ll tell you.” She teased. 

Killian pulled himself up and decided that this was definitely the best night of his life. Like hell he was saying no to this, no matter how tired he was. He always had time for a beautiful woman. 

Sliding into the passenger’s seat, he stared at her. 

“Who are you?” He asked again, hoping that he didn’t look too disheveled. He probably smelled terrible.

“I’m Mrs. Gold.”


	3. First drinking, then David, now this.

**Summary for the Chapter:**

> Milah takes Killian home.

**Notes for the Chapter:**

> OK GUYS so I know I was going to do more with this, but I've unfortunately lost interest in the fic and I don't think I could finish it the way I wanted. HOWEVER I did want to give it a good ending and final chapter, so here you go!!!! :-) THANK YOU ALL for supporting this fic!!!

  
“I’m Mrs. Gold,”

“you can call me Milah.”

Brow furrowed, Killian looks at the woman next to him with confusion.

“I thought that Prof Mills was Mrs. Gold.”

“You’re correct. She was—but the Mills name has more prestige, so she changed it back after the divorce.”

Killian realizes that he’s starting to sober up a little bit, and he’s suddenly very thirsty. A copious amount of alcohol coupled with deep-dick fucking is apparently a combination that favors dehydration. Who knew.

“Oh, so—are you his new wife?” Killian asks, licking his lips and wondering if getting into the car of a strange woman is the stupidest thing he’s ever done. Probably not. Unprotected sex with the quarterback in a parking lock was pretty crazy, too.

He liked it.

“Hell no.” Milah laughs. “I was the first Mrs. Gold. I know—there’s an age difference. I was young and stupid and took the first opportunity I could to skip town. It just happened to be marrying Rupert.”

“We divorced after a few years, and he met Cora. They seemed like a good match. Awful, vindictive people—both divorced—and born within five years of each other! But that didn’t last, either. The new Mrs. Gold just graduated last year. It’s nauseating.”

“There are three of you?” Killian asks, eyebrows up.

“Mr. Gold has had three wives, yes, but we’re not the same.” She informs him. “Although, Cora and I have become fast friends since the divorce. Having dinner together once a week and belittling our ex-husband is a favorite hobby of mine.”

“Why are you telling me this?” Killian asks, slouching back against the seat.

“Because Rupert isn’t the only thing that Cora and I have in common.” Milah explains. “She told me about your night together.”

Killian’s cock is suddenly very interested in what Milah has to say.

“Yeah?” He whispers, ignoring the headache that’s growing the longer he goes without water.

“Yes.” She confirms. “And provided that you give your consent, we’re going to spend the night together. I assume that the football player whose truck you stumbled out of a few minutes ago got you warmed up.”

“Fuck _yes_.” Killian breathes out, glad that the alcohol is pretty much out of his system. He wants to be sober for this. He wants to remember.

“Do you remember how things were with Cora?” She continues. “If you say no, we will stop. If you disobey me, you will be punished. I won’t hurt you, but that doesn’t mean you won’t feel pain. Are we clear?”

Killian can only nod.

“Wonderful.” She smirks, cocks an eyebrow, and gives him a once-over before returning her eyes to the road. “Tell me what he did to you.”

“What?...”

“The football player.” She pauses. “Tell me exactly what he did—oh, and here.” She briefly reaches into the backseat, pulling out a six-pack of bottled water and dropping it unceremoniously in his lap. “There are painkillers in the glove compartment.”

Killian swallows a few pills and chugs a bottle of water before continuing.

“We fucked—obviously.”

“That doesn’t tell me anything. What did he do to you?”

“He, uh…well, he fucked me.” Killian half-mutters, suddenly embarrassed. “That’s why we were in the truck.”

“And who put that idea in his head? I’ve heard that the quarterback—what’s his name, David?—is rather devoted to his piccolo-playing girlfriend.”

“Yeah, well…it may have been my idea.” Killian admits, opening a second bottle of water because there’s no way in hell that he’s letting himself get hung-over when there’s a night with a beautiful woman at stake.

Milah pulls over to get gas, and he makes a beeline for the restroom. They’re on the road again a few minutes later, and Killian feels much better now that his bladder is empty.

“Keep talking.” Milah instructs once they’re back on the road. They’re not on the highway anymore. Killian hopes that they’re almost to their destination. “How did it feel?”

“How do you th—I mean, good.” Killian looks out the window, his face burning. “It felt good.”

“Did it? Did it feel good when he shoved himself into you? How long were you waiting—how long have you been waiting—for someone to fuck you again? Has it been the only thing on your mind since you let my _dear_ Cora bend you over?”

Killian just sort of whimpers, because he’s well on the way to getting hard.

“Oh? You want me to keep talking?” Milah laughs, slowing down. The car stops a minute later and he realizes that she’s pulled over at a wayside. “I imagine that he was bigger than what Cora used on you. Your first time getting fucked was with her, from what I heard—she probably didn’t want to break you just yet.” She unbuckles her seatbelt and looks over at the man next to her. “Tell me about his cock.”

“It was bigger.” Killian confirms, meeting her gaze with a red face. “It hurt more, but—“

“But you liked it?” The grin on her face is positively evil.

“Yes.” He admits, hard in his jeans.

“Unzip, touch yourself, and tell me what you want me to do to you.”

He’s quick to undo his jeans and pull out his cock, giving himself a few quick strokes. Letting out a relieved groan, he takes in the way that Milah is looking at him. She almost looks disinterested, like instead of a young man masturbating next to her there’s a fucking houseplant.

He didn’t think it was possible to get harder than this.

“I…”

“I understand if it’s hard to start talking, but if you won’t play I’m taking you home.”

“I’m still sore.” He blurts out. “I can still feel how—just—that he fucked me. It still hurts a little but I don’t care. I want to know what it would feel like to have you fuck me, too.”

“Good boy.” She whispers, and the praise makes him whimper. “Twice in one night? You’re so needy. I knew you would be—that’s why I pulled over to pick you up. I didn’t think you could last until we got home, so I thought ahead.”

“What do you mean?” He asks, stroking himself and looking at her.

Reaching into the backseat, she pulls out her purse and opens it. “I can’t have you coming before we’re ready, and I won’t have you putting the quarterback’s hard work to waste. Put this on.”

He stares at the cock ring.

“But I want to c—“

“You’ll come when I want you to. I know what’s best for you, is that clear?” Her voice is steel, and it’s hard for him to still his head.

“Yes.” He frowns and takes it from her, rolling it onto his erection and wondering how long he’s going to have to stay like this.

“Don’t worry, that’s not the only present I have for you.”

What she holds up next makes his face pale.

“That’s too b—“

“I want you ready for me as soon as I pull into my driveway. Now get out of the car.”

“I—“

“ _Now_.”

He obeys, and soon enough they’re standing in front of the vehicle. His eyes are still trained on the plug in her hand. The thickest part of it is bigger than David’s cock.

“Bend over and take off your pants.”

They’re in public. It’s three in the morning and the wayside is deserted and she’s parked out of sight, but they’re in _public_.

If he wasn’t wearing the cock ring, he would have come by now. Of that, Killian is certain. Quick to please her, he drops his pants and leans over the car, arms crossed.

“Good boy.” She says approvingly, giving his ass a slap that’s nothing but gentle. He cries out, and thinks, with no irony, that this is _great_.

“Look at you. Still a little slick from David.” She spreads his cheeks and he presses his hot face against the cool hood of the car. “This is going to be a little cold.”

He hears what he assumes is a bottle of lube open, and there are wet fingers against his hole a few seconds later. Moaning, he rocks back against them.

“I had no idea you were this much of a slut.” Milah laughs, two fingers inside of him. They spread and they curl and they— _damn_ —there’s a third. He loves this. He loves it.  He wants more, a—

“I know, baby. I know.” She fusses, and he realizes that he’s been saying all of this out loud. “It’s not enough, is it?”

“No…” He whines, rolling his hips and trying to fuck himself on the four fingers that are shoved into him.

“Don’t worry, darling. I have what you need.” The fingers come out and he groans in frustration, feeling exposed and empty. A few seconds later the head the plug is pressing against his loosened hole, and he immediately moves his hips to try and take it in.

She places a hand on his lower back to keep him still. It’s hard not to move, but he manages. Far too slowly for his liking, she pushes the toy forward. It keeps getting thicker the further in it gets, and soon he’s being stretched open more than ever before.

It hurts. Killian’s cock is leaking against the hood of the car. He can’t keep down the surprised noise that escapes his throat as the plug enters him completely. It’s a very different experience than the strap-on, or even David’s cock. It’s just _in_ him. There’s nothing fucking him. He’s just _full_.

“Such a good boy. I didn’t think you’d be this well behaved.” She places a soft, gentle kiss to the small of his back. A reward. “Now pull your pants back up, and let’s go.”

Legs weak, he stands and bends over to pull his jeans back up. He’s still hard thanks to the ring around the base of his cock, and now that the plug is keeping him open it feels like he’s perpetually stuck in mid-fuck. He just wants to come, or at least stick his dick in something.

As he gingerly sits back down and fastens his seatbelt, he sees that Milah is smiling.

“We’re taking the long way home.” She explains, starting the engine.

It turns out what that means is that they’re taking a poorly maintained back-road that’s probably very out of the way. With each bump and pothole, the plug presses into him and he goes even more aware of his hard, aching cock.

By the time that they finally pull into what he _prays_ is her driveway, he’s never wanted to come so badly in his life.

It seems like Milah can tell, because she’s still got a wicked grin on her face.

“I’m sorry, was the road too bumpy for you?” She laughs, getting out of the car. He’s quick to follow, his jeans uncomfortably tight. She hadn’t let him unbutton them. “Don’t worry, you’ll be taken care of. Eventually.”

Once they’re inside, he moves to kiss her, but she pushes him away.

“Oh, no. You’re the one we’re taking care of. You don’t get to touch me.” She laughs. “Follow me. I have a surprise for you.”

They get to what he assumes is the living room, and his eyes widen in surprise.

Sitting in what looks like a very expensive leather couch is Professor Mills herself, fully clothed with her legs crossed.

“You’re both going to fuck me?” He asks excitedly, thinking of all of the things that they could do to him. A cunt in his face, something silicone in his ass. _Four_ tits to get his mouth on.

“No, of course not, you stupid little boy. As if you’re worth that.” Cora sneers, and Killian’s so aroused that he thinks he might just die. “We’re going to watch.”

“What?” He looks to Milah for an explanation. The first Mrs. Gold seems more forgiving than the second. Maybe she’ll explain.

“Between Cora and that football player you’ve really been quite selfish.” She explains. “Letting them do all the work. It’s time that you learned to provide for yourself.”

Killian’s eyes move to the coffee table, where a semi-realistic (it has a base that’s clearly been modeled after testicles) red dildo is proudly sitting.

“Take the plug out, and fuck yourself where we can see.” Milah sits down next to Cora. “If you’re a good little boy, we might even let you come.”

“It’s…” He blushes because he still doesn’t know how to talk about this. The dildo, though a reasonable length, is as thick as the widest part of the plug he’s still wearing, and he’s not sure if he can take it.

“Big? We know—but if we didn’t think you could do this, we wouldn’t have invited you here. Now take off your clothes.”

He isn’t sure which woman just spoke to him, he’s too busy thinking about what he’s going to do. Hands dropping to his waist, he lets his pants fall to the ground and steps out of them, groaning as cool air hits his dick. The sweatshirt and ratty old t-shirt he’d warn to the bar soon follow, but all he can focus on his how much he needs to be _fucked_ , not just have the plug keeping him full and open.

“Turn around and bend over. Let me see.” Cora says calmly, and all that he can do is listen to her. There’s a soft rug—some kind of fur, he doesn’t really care what animal it came from so long as it won’t hurt his knees—in front of the coffee table. That’s where he kneels.

“Arch your back and lean down, I want to see you properly.”

The funny thing is that Cora’s speaking the same way that she would in a classroom. He can’t tell whether or not she’s actually getting turned on, or if this is just another opportunity to teach. Honestly, Killian can’t tell which possibility is more arousing. A brief fantasy of eating Cora out as she lectures flits through his mind, and he lets out a sound he’d be embarrassed about under other circumstances.

Instead of making a sarcastic comment, he does as he’s told and nearly starts crying because he’s never been denied an orgasm like this, and it hurts and he _needs_ more.

“Good.” Cora grins. “Now take it out. Slowly.”

He reaches back and gives the toy a tug, groaning when he feels resistance, the body of the plug too thick to slide easily out of him. He pulls at it a few more times, and it’s not nearly as satisfying as a cock would be, and on the third or fourth try it comes out and he can’t help but moan.

“Put it down on the table.” Cora whispers.

He does.

“How do you feel?” Milah asks.

“I need more.” He whispers, face burning as he hides it in the crook of his elbow. “I want to come.”

“If you’re good.” Cora tut-tuts. “Now do what we’ve told you.”

Sitting up a little, he reaches over and picks up the dildo, looking at it and swallowing hard.

“Well? What are you waiting for? Are you so stupid that you don’t know where it goes?” Cora scolds. Her words feed his arousal. This is the same way that she spoke to him after he failed his first exam, before she’d realized that he was a lost cause.

Reaching back, he presses the head of the silicone cock against himself. It feels big, but his hole is still wet and ready from what Milah did to him at the wayside, and he manages to get it in fairly quickly.

There’s pain, he can’t deny it. When he’d let David fuck him, they’d both been drunk, and not as careful as they should have been. He’d have been sore anyway. Killian can’t even imagine what the next morning is going to feel like after this. Hell, this probably isn’t all that the two women have planned.

He wonders what else they’re going to do, and wishes that someone would suck him off, or at least touch him. At all. Even a hand in his hair, on his face—anything.

“Touch me.” He cries before he can stop himself, cock hot and heavy between his legs.

“No. Why would we? What have you earned? Do you even have any idea what you’re doing?” Milah’s voice is soft. “Fucking yourself like a horny freshman? It’s obvious that you don’t know what you’re doing.”

“You’re so clumsy.” Cora adds. “It’s pathetic, really. I expected more from you. You know what you want, but you have no idea how to go about getting it. Haven’t you paid _any_ attention when you stick that sorry excuse for a prick into any hole that will take you?”

He starts moving the toy, and it’s satisfying but _not enough._ The angle is awkward and even though he’s in shape, he knows that his arm is going to get tired before long.

“I really thought you’d be better at this. I’m disappointed.” Milah says idly.

“I’m afraid to say that I agree. I was promised a good show, and you’re letting both of us down. Apologize.” Cora’s scolds.

“I’m sorry!” He says immediately, because maybe if he does everything that they say, they’ll let him take off the cock-ring—or at least fuck him.

“For what?”

“For not being good enough—for not knowing how to fuck myself. I’m sorry.” He whimpers, desperately working the toy against his hole in an attempt to reach an orgasm he knows won’t be allotted to him until he’s been good enough.

“I can’t hear you. Louder.” Cora whispers, her voice low. He glances over his shoulder and sees that Cora’s hand is up under Milah’s skirt. Oh god. _Oh god_. This is all for them. He’s nothing more than a toy to them—a show—not even a person. Just a stupid little boy.

He’s actually crying now. There are tears on his face, and his breathing is harsh and ragged.

“I’m sorry!” He nearly wails. “I’m sorry—I’ll do better if you let me come, I promise. _I promise!_ ”

“You’re pitiful.” Cora scoffs. “I’m upset with you. I didn’t think you’d be begging like this so soon. I’m inclined to put you out of your misery just to make it stop. However, if we let you come, we’re going to have to punish you.”

“Please!” He begs.

“Please what?”

“Please let me come—please punish me—please fuck me—just— _please—“_

 _“Fine.”_ Cora sighs. “Get onto your back and put your arms above your head. Don’t touch yourself. Milah will help you.”

Doing as he’s told, Killian rolls onto his back. He lets go of the toy—but it’s still inside of him—and puts his arms up.

Milah knees between his legs and grabs the base of the toy, fucking him surprisingly hard. She’s strong. Her other hand rolls off the cock-ring, and he’s seeing stars.

“She wasn’t even touching that thing you call a cock. Pathetic.” Cora laughs afterwards, when he’s lefty panting and sweating on the rug. It’s true. Milah’s fingers hadn’t been on him when he’d come—the amount of time he’d been denied and the dildo in his ass had been enough.

“I’m afraid I have to agree. You need to be punished.” Milah steps back and pulls open a drawer in the coffee table, taking out yet another toy. This one falls somewhere between the two that have been used on him today.

It’s ridged and thick, but it gets thinner just before the base. They could either fuck him with it, or leave it in him as long as they wanted.

“On your knees. Ass up.” Milah says calmly, and Killian obeys. He’s sore and sensitive after his orgasm, and he’s acutely aware of each swell of the new toy as it’s slowly pushed into his abused hole and left there. “Does it hurt?”

“Yes.” Killian admits. “It’s big, I—“

“You deserve this. You should have been able to hold out longer. Now hold still.”

Cora’s behind him too, now.  She brings her hand back, and it lands hard on his ass. The pain doesn’t really bother him. Then she hits him again.

And again.

And again.

His ass is raw and red, and _how_ isn’t her hand sore?

“Do you want more?”

He doesn’t respond, too caught up in how it feels.

“I said, _do you want more_?”

“Yes! Yes, ma’am!” He cries out. It’s true. As much as it hurts, he does want more.

“Good. Turn around.”

He moves onto his back, and realizes that he’s hard again as Cora rolls the ring back on. All he can do is let out a whimper as Milah twists one of his nipples.

“I didn’t think you’d give in this easily. I thought you were stronger.” She sounds so let down, and he feels horrible.

“I’m sorry.” He whimpers.

“Are you ready to prove it?” Cora asks.

Killian nods, a shiver going down his spine as the professor gives his cock a harsh pull. “Yes!”

“Here’s what’s going to happen, dear.” She explains, running gentle fingers through his hair. Milah starts to lazily fuck him with the toy in his ass, the fingernails of her other hand dug into the bruises that Cora has left on his backside. “We’re going to tie you up, and leave you all alone so that you can think about what you’ve done.

“But I want you here—“

“That’s why it’s a _punishment_. You’re not meant to like it.”

All that Killian can really do is nod helplessly, gripping the rug underneath him and watching Cora as she opens the drawer out again and pulls out a pair of handcuffs and a length of rope.

“Knees to your chest.”

He does as he’s told. Cora takes his hands and brings them around his thighs so that he’s pulling his legs up with his arms. She fastens the cuffs, and he realizes that it’s now impossible to lower his legs.

Her next move is to bind his elbows to his knees so that his legs stay spread. It’s simple, and he could wiggle away if he really tried…but he won’t.

“We’ll untie you after you’ve had time to think.” Cora explains. “Do you have any questions?”

“When do I get to come?” Killian asks immediately. No one’s fucking him now so he’s not quite as desperate, but he’s very conscious of how open his legs are and how full of cock (albeit silicone) he is.

“You don’t.” Milah says immediately. That shouldn’t be as hot as it is. “But if you behave, we might take you back in the future. Now think about what you can do to be more patient, if we decide that you’ve _really_ tried we might invite you back here one day.”

The two women leave, and his thoughts immediately go to what they might be doing to each other.

Killian assumed that they’d be back in twenty minutes, but it’s at least two hours until they reappear. The sun is probably starting to come out—it’s been a long night. First drinking, then David, now _this_.

“My, my. I am impressed.” Cora says immediately, and Killian swells with pride. “I thought you’d start complaining less than an hour in.”

“I want to do better.” He says honestly, because it’s true. Every fiber of his being, even now when he’s been left alone this long, just wants to please them. “Please take me back.”

“You’re being very good.” The praise spreads through him from head to toe. Those four simple words leave him feeling warm and breathless. He wants more.

Cora starts to untie him. “If you keep this up, if you continue to behave, you’ll get what you want sooner than you think.”

After making sure that he’s hydrated and in good health, they take him home. As he, exhausted, watches them drive away, there’s only one thought in his head.

He could get used to this. 

**Author's Note:**

> This fic has been my dream for awhile. I'd like to think my amazing beta GraveVyxen for being amazing and A+. Ya'll should check her out! Also, not every chapter will be this long--but I always get carried away when I write Cora/Hook. Enjoy! Also, I had to change the title to make it appropriate for ff.net. Enjoy.


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